This Is AuburnElectronic Theses and Dissertations

Allylic Oxidation of Steroidal Compounds Using Vanadyl Acetylacetonate and Tert-butyl Hydroperoxide

Date

2015-07-29

Author

Grainger, Wendell

Type of Degree

Dissertation

Department

Chemistry and Biochemistry

Abstract

Allylic oxidation is an important reaction in steroid chemistry. Previously reported methods have various limits which do not apply when using vanadyl acetylacetonate and tert-butyl hydroperoxide. These limits include costs, need for inert environments, short half-lives of catalysts, over-oxidation, need for protection groups, and low yields. Vanadyl acetylacetonate is inexpensive and shelf stable. Here, we describe the novel use of vanadyl acetylacetonate for oxidation of a variety of ∆5 steroidal olefins, without protection groups, in ambient atmosphere and at room temperature.